N-(3-Chloro­phen­yl)acetamide

Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536807068808

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o381

doi:10.1107/S1600536807068808

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N-(3-Chlorophenyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 25 December 2007; accepted 31 December 2007; online 9 January 2008)

The conformation of the N—H bond in the structure of the title compound (3CPA), C₈H₈ClNO, is anti to the meta-chloro substituent, in contrast to the syn conformation observed for the ortho-chloro substituent in N-(2-chlorophenyl)acetamide, syn to both the ortho and meta chloro substituents in N-(2,3-dichlorophenyl)acetamide, and syn to the ortho chloro substituent in N-(2,4-dichlorophenyl)acetamide. There are two molecules, linked by an N—H⋯O hydrogen bond, in the asymmetric unit of 3CPA. The bond parameters in 3CPA are similar to those of other acetanilides and the molecules are packed into chains through intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2006 ); Gowda, Foro & Fuess (2007 ); Gowda, Svoboda & Fuess (2007 ); Pies et al. (1971 ).

Experimental

Crystal data

C₈H₈ClNO
M_r = 169.60
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.8468 (8) Å
b = 18.562 (2) Å
c = 18.852 (3) Å
V = 1696.0 (4) Å³
Z = 8
Cu Kα radiation
μ = 3.51 mm⁻¹
T = 299 (2) K
0.60 × 0.15 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.225, T_max = 0.756
3119 measured reflections
2780 independent reflections
2098 reflections with I > 2σ(I)
R_int = 0.019
3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.224
S = 1.07
2780 reflections
207 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.59 e Å⁻³
Absolute structure: Flack (1983 ), 987 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86 (2)	2.00 (2)	2.846 (5)	166 (6)
N2—H2N⋯O1	0.830 (19)	2.11 (2)	2.927 (5)	167 (6)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068808/dn2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068808/dn2306Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(3-chlorophenyl)-acetamide (3CPA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda, Foro & Fuess, 2007; Gowda, Svoboda & Fuess, 2007). The conformation of the N—H bond in the structure of 3CPA (Fig. 1) is anti to the meta-chloro substituent in contrast to the syn conformation observed for the ortho-chloro substituent in N-(2-chlorophenyl)-acetamide (2CPA)(Gowda, Svoboda & Fuess, 2007), syn to both the ortho and meta Chloro substituents in N-(2,3-dichlorophenyl)-acetamide(23DCPA)(Gowda, Foro & Fuess, 2007) and syn to the ortho-chloro substituent in N-(2,4-dichlorophenyl)-acetamide (24DCPA)(Gowda, Svoboda & Fuess, 2007). The structure of 3CPA has two molecules linked by N—H···O hydrogen bond in its asymmetric unit. The geometric parameters of 3CPA are similar to those of 2CPA, 23DCPA, 24DCPA and other acetanilides (Gowda, Foro & Fuess, 2007; Gowda, Svoboda & Fuess, 2007). The molecules are linked by hydrogen bonds, N1H1NO2 and N2H2NO1 with respective H1N O2 and H2N O1 lenghts of 2.00 and 2.11 Å, and the angles, N1 H1N O2 and N2 H2N O1 of 166 and 167 °, respectively (Table 1 & Fig. 2).

Related literature top

For related literature, see: Gowda et al. (2006); Gowda, Foro & Fuess (2007); Gowda, Svoboda & Fuess (2007); Pies et al. (1971).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2006). The purity of the compound was checked by determining its melting point. The compound was characterized by recording its infrared,NMR and NQR spectra (Gowda et al., 2006 and Pies et al., 1971). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) -x, y - 1/2, 1/2 - z]

N-(3-Chlorophenyl)acetamide top

Crystal data top

C₈H₈ClNO	F(000) = 704
M_r = 169.60	D_x = 1.328 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 4.8468 (8) Å	θ = 4.8–19.8°
b = 18.562 (2) Å	µ = 3.51 mm⁻¹
c = 18.852 (3) Å	T = 299 K
V = 1696.0 (4) Å³	Needle, colourless
Z = 8	0.60 × 0.15 × 0.08 mm

Data collection top

Enraf–Nonius CAD4 diffractometer	2098 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 67.0°, θ_min = 3.3°
ω/2θ scans	h = −5→0
Absorption correction: ψ scan (North et al., 1968)	k = −22→0
T_min = 0.225, T_max = 0.757	l = −22→14
3119 measured reflections	3 standard reflections every 120 min
2780 independent reflections	intensity decay: 2.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.082	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.224	w = 1/[σ²(F_o²) + (0.1656P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
2780 reflections	Δρ_max = 0.43 e Å⁻³
207 parameters	Δρ_min = −0.59 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 987 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

Crystal data top

C₈H₈ClNO	V = 1696.0 (4) Å³
M_r = 169.60	Z = 8
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 4.8468 (8) Å	µ = 3.51 mm⁻¹
b = 18.562 (2) Å	T = 299 K
c = 18.852 (3) Å	0.60 × 0.15 × 0.08 mm

Data collection top

Enraf–Nonius CAD4 diffractometer	2098 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.019
T_min = 0.225, T_max = 0.757	3 standard reflections every 120 min
3119 measured reflections	intensity decay: 2.0%
2780 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.224	Δρ_max = 0.43 e Å⁻³
S = 1.07	Δρ_min = −0.59 e Å⁻³
2780 reflections	Absolute structure: Flack (1983), 987 Friedel pairs
207 parameters	Absolute structure parameter: 0.00 (4)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.3831 (6)	0.37160 (11)	0.39860 (11)	0.1367 (10)
O1	−0.0630 (10)	0.23187 (18)	0.2036 (2)	0.0880 (12)
N1	0.0399 (8)	0.14104 (19)	0.2789 (2)	0.0641 (10)
H1N	0.028 (12)	0.0957 (12)	0.288 (3)	0.077*
C1	0.2186 (9)	0.1757 (2)	0.3267 (3)	0.0609 (11)
C2	0.2211 (11)	0.2491 (3)	0.3358 (3)	0.0687 (13)
H2	0.1068	0.2782	0.3084	0.082*
C3	0.3931 (14)	0.2792 (4)	0.3853 (3)	0.0854 (17)
C4	0.5720 (14)	0.2367 (6)	0.4257 (4)	0.108 (3)
H4	0.6915	0.2575	0.4584	0.130*
C5	0.5665 (16)	0.1649 (6)	0.4158 (4)	0.116 (3)
H5	0.6851	0.1359	0.4421	0.139*
C6	0.3871 (13)	0.1324 (4)	0.3669 (3)	0.0868 (16)
H6	0.3823	0.0825	0.3619	0.104*
C7	−0.0907 (10)	0.1695 (2)	0.2219 (3)	0.0608 (11)
C8	−0.2696 (12)	0.1186 (3)	0.1825 (3)	0.0804 (15)
H8A	−0.2326	0.0703	0.1980	0.121*
H8B	−0.2325	0.1225	0.1326	0.121*
H8C	−0.4597	0.1301	0.1913	0.121*
Cl2	0.6744 (5)	0.49383 (10)	−0.03716 (11)	0.1181 (8)
O2	0.0909 (9)	0.49682 (17)	0.1824 (2)	0.0865 (12)
N2	0.1055 (8)	0.37741 (16)	0.1625 (2)	0.0552 (9)
H2N	0.085 (12)	0.3348 (13)	0.175 (3)	0.066*
C9	0.3111 (8)	0.3741 (2)	0.1092 (2)	0.0493 (9)
C10	0.3766 (11)	0.4316 (2)	0.0668 (3)	0.0635 (12)
H10	0.2864	0.4756	0.0715	0.076*
C11	0.5868 (12)	0.4215 (3)	0.0158 (3)	0.0679 (13)
C12	0.7118 (10)	0.3568 (3)	0.0071 (3)	0.0675 (12)
H12	0.8437	0.3510	−0.0283	0.081*
C13	0.6462 (10)	0.3011 (3)	0.0493 (3)	0.0673 (13)
H13	0.7374	0.2573	0.0441	0.081*
C14	0.4402 (9)	0.3086 (2)	0.1013 (3)	0.0587 (11)
H14	0.3920	0.2698	0.1300	0.070*
C15	0.0080 (9)	0.4367 (2)	0.1948 (3)	0.0593 (11)
C16	−0.2118 (12)	0.4235 (3)	0.2501 (3)	0.0800 (15)
H16A	−0.2754	0.3746	0.2467	0.120*
H16B	−0.3636	0.4558	0.2423	0.120*
H16C	−0.1362	0.4317	0.2964	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.172 (2)	0.1231 (14)	0.1148 (14)	−0.0737 (15)	0.0260 (16)	−0.0395 (11)
O1	0.094 (3)	0.0659 (19)	0.104 (3)	−0.0177 (19)	−0.023 (2)	0.0274 (19)
N1	0.057 (2)	0.0524 (18)	0.082 (3)	−0.0095 (16)	−0.003 (2)	0.0140 (19)
C1	0.041 (2)	0.075 (3)	0.067 (3)	−0.0049 (19)	0.003 (2)	0.008 (2)
C2	0.058 (3)	0.078 (3)	0.070 (3)	−0.014 (2)	0.005 (3)	0.003 (2)
C3	0.068 (4)	0.115 (4)	0.073 (3)	−0.034 (3)	0.023 (3)	−0.011 (3)
C4	0.053 (3)	0.188 (8)	0.083 (4)	−0.032 (4)	−0.001 (3)	−0.026 (5)
C5	0.075 (4)	0.176 (8)	0.097 (5)	0.034 (5)	−0.025 (4)	−0.007 (5)
C6	0.070 (3)	0.104 (4)	0.086 (4)	0.020 (3)	−0.010 (3)	0.007 (3)
C7	0.054 (2)	0.055 (2)	0.073 (3)	−0.0023 (19)	−0.003 (2)	0.009 (2)
C8	0.062 (3)	0.085 (3)	0.093 (4)	−0.013 (3)	−0.010 (3)	0.001 (3)
Cl2	0.1326 (17)	0.1002 (11)	0.1217 (13)	−0.0127 (11)	0.0357 (13)	0.0404 (10)
O2	0.086 (3)	0.0506 (16)	0.123 (3)	0.0048 (19)	0.018 (2)	−0.0152 (18)
N2	0.0491 (18)	0.0411 (15)	0.075 (2)	−0.0052 (15)	0.0041 (19)	−0.0026 (16)
C9	0.0391 (18)	0.0504 (19)	0.058 (2)	−0.0029 (15)	−0.0012 (19)	−0.0094 (18)
C10	0.058 (3)	0.051 (2)	0.081 (3)	0.005 (2)	0.004 (2)	0.006 (2)
C11	0.067 (3)	0.071 (3)	0.066 (3)	−0.016 (2)	0.001 (3)	0.007 (2)
C12	0.047 (2)	0.081 (3)	0.075 (3)	−0.002 (2)	0.007 (2)	−0.007 (3)
C13	0.040 (2)	0.072 (3)	0.090 (3)	0.009 (2)	0.008 (2)	−0.009 (2)
C14	0.051 (2)	0.050 (2)	0.075 (3)	−0.0008 (18)	−0.003 (2)	0.001 (2)
C15	0.052 (2)	0.053 (2)	0.073 (3)	0.0010 (18)	0.000 (2)	−0.007 (2)
C16	0.054 (3)	0.089 (3)	0.097 (4)	0.004 (2)	0.012 (3)	−0.015 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.735 (7)	Cl2—C11	1.726 (5)
O1—C7	1.215 (5)	O2—C15	1.209 (6)
N1—C7	1.355 (6)	N2—C15	1.343 (5)
N1—C1	1.406 (6)	N2—C9	1.416 (5)
N1—H1N	0.86 (2)	N2—H2N	0.830 (19)
C1—C2	1.373 (7)	C9—C10	1.371 (6)
C1—C6	1.375 (7)	C9—C14	1.376 (6)
C2—C3	1.371 (8)	C10—C11	1.414 (8)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.397 (11)	C11—C12	1.354 (7)
C4—C5	1.347 (12)	C12—C13	1.343 (7)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.403 (10)	C13—C14	1.407 (7)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.482 (7)	C15—C16	1.511 (7)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600

C7—N1—C1	128.1 (4)	C15—N2—C9	127.2 (4)
C7—N1—H1N	121 (4)	C15—N2—H2N	128 (4)
C1—N1—H1N	111 (4)	C9—N2—H2N	104 (4)
C2—C1—C6	120.5 (5)	C10—C9—C14	121.3 (4)
C2—C1—N1	122.6 (4)	C10—C9—N2	122.9 (4)
C6—C1—N1	116.8 (5)	C14—C9—N2	115.8 (4)
C3—C2—C1	119.6 (6)	C9—C10—C11	117.4 (4)
C3—C2—H2	120.2	C9—C10—H10	121.3
C1—C2—H2	120.2	C11—C10—H10	121.3
C2—C3—C4	121.3 (7)	C12—C11—C10	121.5 (4)
C2—C3—Cl1	118.9 (6)	C12—C11—Cl2	120.6 (4)
C4—C3—Cl1	119.8 (6)	C10—C11—Cl2	117.8 (4)
C5—C4—C3	118.1 (6)	C13—C12—C11	120.3 (5)
C5—C4—H4	121.0	C13—C12—H12	119.8
C3—C4—H4	121.0	C11—C12—H12	119.8
C4—C5—C6	121.9 (7)	C12—C13—C14	120.4 (4)
C4—C5—H5	119.0	C12—C13—H13	119.8
C6—C5—H5	119.0	C14—C13—H13	119.8
C1—C6—C5	118.6 (6)	C9—C14—C13	119.0 (4)
C1—C6—H6	120.7	C9—C14—H14	120.5
C5—C6—H6	120.7	C13—C14—H14	120.5
O1—C7—N1	123.0 (5)	O2—C15—N2	123.5 (5)
O1—C7—C8	122.0 (5)	O2—C15—C16	121.1 (4)
N1—C7—C8	114.9 (4)	N2—C15—C16	115.4 (4)
C7—C8—H8A	109.5	C15—C16—H16A	109.5
C7—C8—H8B	109.5	C15—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C7—C8—H8C	109.5	C15—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5

C7—N1—C1—C2	21.1 (8)	C15—N2—C9—C10	−22.1 (7)
C7—N1—C1—C6	−161.3 (5)	C15—N2—C9—C14	159.1 (5)
C6—C1—C2—C3	0.0 (8)	C14—C9—C10—C11	−1.5 (7)
N1—C1—C2—C3	177.5 (5)	N2—C9—C10—C11	179.8 (4)
C1—C2—C3—C4	1.8 (8)	C9—C10—C11—C12	2.4 (8)
C1—C2—C3—Cl1	−177.4 (4)	C9—C10—C11—Cl2	−179.1 (4)
C2—C3—C4—C5	−1.6 (10)	C10—C11—C12—C13	−2.8 (8)
Cl1—C3—C4—C5	177.5 (6)	Cl2—C11—C12—C13	178.8 (4)
C3—C4—C5—C6	−0.3 (12)	C11—C12—C13—C14	2.2 (8)
C2—C1—C6—C5	−1.8 (9)	C10—C9—C14—C13	0.9 (7)
N1—C1—C6—C5	−179.4 (6)	N2—C9—C14—C13	179.8 (4)
C4—C5—C6—C1	2.0 (11)	C12—C13—C14—C9	−1.3 (7)
C1—N1—C7—O1	1.5 (8)	C9—N2—C15—O2	−1.2 (8)
C1—N1—C7—C8	−179.1 (5)	C9—N2—C15—C16	−179.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86 (2)	2.00 (2)	2.846 (5)	166 (6)
N2—H2N···O1	0.83 (2)	2.11 (2)	2.927 (5)	167 (6)

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₈ClNO
M_r	169.60
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	299
a, b, c (Å)	4.8468 (8), 18.562 (2), 18.852 (3)
V (Å³)	1696.0 (4)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	3.51
Crystal size (mm)	0.60 × 0.15 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.225, 0.757
No. of measured, independent and observed [I > 2σ(I)] reflections	3119, 2780, 2098
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.224, 1.07
No. of reflections	2780
No. of parameters	207
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.59
Absolute structure	Flack (1983), 987 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86 (2)	2.00 (2)	2.846 (5)	166 (6)
N2—H2N···O1	0.830 (19)	2.11 (2)	2.927 (5)	167 (6)

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

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